| 1 | 24/8/2019 | 18 2-0 v UxbridgeSittingbourne 2-0 Uxbridge | Emirates FA Cup Preliminary Round |
| 2 | 26/8/2019 | 152-1 v RamsgateRamsgate 1-2 Sittingbourne | BetVictor Isthmian South East Division |
| 3 | 3/9/2019 | 102-2 v Sevenoaks TownSevenoaks Town 2-2 Sittingbourne | Velocity Trophy Group 9 |
| 4 | 17/9/2019 | 141-2 v Ashford UnitedAshford United 2-1 Sittingbourne | BetVictor Isthmian South East Division |
| 5 | 21/9/2019 | 70-1 v GuernseySittingbourne 0-1 Guernsey | BetVictor Isthmian South East Division |
| 6 | 24/9/2019 | 114-4 v VCD AthleticSittingbourne 4-4 VCD Athletic | Velocity Trophy Group 9 |
| 7 | 12/10/2019 | 161-0 v South ParkSittingbourne 1-0 South Park | Buildbase FA Trophy Preliminary Round |
| 8 | 15/10/2019 | 171-1 v RamsgateSittingbourne 1-1 Ramsgate | Kent Senior Cup First Round |
| 9 | 19/10/2019 | 171-0 v Hythe TownSittingbourne 1-0 Hythe Town | BetVictor Isthmian South East Division |
| 10 | 22/10/2019 | 174-2 v Phoenix SportsPhoenix Sports 2-4 Sittingbourne | Velocity Trophy Group 9 |
| 11 | 26/10/2019 | 170-1 v Tooting & Mitcham UnitedSittingbourne 0-1 Tooting & Mitcham United | Buildbase FA Trophy First Qualifying Round |
| 12 | 5/11/2019 | 143-2 v Cray Valley PMSittingbourne 3-2 Cray Valley PM | Velocity Trophy Group 9 |
| 13 | 9/11/2019 | 172-0 v Herne BaySittingbourne 2-0 Herne Bay | BetVictor Isthmian South East Division |
| 14 | 16/11/2019 | 171-1 v Chichester CityChichester City 1-1 Sittingbourne | BetVictor Isthmian South East Division |
| 15 | 23/11/2019 | 172-1 v VCD AthleticSittingbourne 2-1 VCD Athletic | BetVictor Isthmian South East Division |
| 16 | 30/11/2019 | 171-2 v Burgess Hill TownBurgess Hill Town 2-1 Sittingbourne | BetVictor Isthmian South East Division |
| 17 | 7/12/2019 | 162-1 v Sevenoaks TownSevenoaks Town 1-2 Sittingbourne | BetVictor Isthmian South East Division |
| 18 | 10/12/2019 | 150-1 v Hastings UnitedSittingbourne 0-1 Hastings United | BetVictor Isthmian South East Division |
